تفاعل #45667

معادلة التفاعل

dimethyl sulfoxide

(3R)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

N-[2-(tert-butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

triethylamine

→

compound

المردود 42.0%

4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]N-(2-hydroxyethyl)-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

المردود 42.0%

المذيبات

brine

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction liquid
2. 2
   استخلاصwas extracted with ethyl acetate
3. 3
   غسيلNext, the combined organic layer was washed with saturated brine
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزthe filtrate was concentrated under reduced pressure

الإجراء التجريبي

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3R)-3-(dimethylamino)pyrrolidine (76 μl, 598 μmol) was added at 150° C. to a dimethyl sulfoxide (9 ml) solution of N-[2-(tert-butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-124) (295 mg, 499 μmol) and triethylamine (90 μl, 649 μmol), followed by stirring at the same temperature for 20 minutes. After pooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (10:1, v/v) gave the entitled compound (93 mg, 42%) as an amorphous substance.

المصدر